Gold Member

Who else had a "Mrs Robinson" figure in their youth. She was the prototype for the MILF for those of us that remember the Graduate more than American Pie.

Mine was a recent recent divorcee, whose daughter was dating my best friend. She was in her late 30's, but was still really pretty. She and her ex had some money and she'd used those resources to keep herself in pretty good shape.

I had been around a few times, basically stopping to pick up the daughter. When she heard that I did lawn work, she asked if I would help her get her back yard under control. She had gotten a pretty good sized house and yard in the divorce, but she hadn't really been taking care of it.

It actually took me a couple times to see where it was headed. But lemonade in the yard turned into lemonade at the table and then a beer on the couch. Yes, she actually plied me with alcohol to take a way some of my teenage nerves.

I ended up having sex with her the rest of the summer. Most of the time I had to work first. When I came back on break she had a new boyfriend and he was taking care of the yard. It was still a heck of a summer job.

VerifiedGold Member

My first experience with a MILF came when I was 17 before my senior year in H.S. Was working in the local vet clinic. This older woman, very attractive with a nice bod, brought her dog in to have it neutured. She walked back to the holding cages with me and I knelt down to put her dog in a lower cage. Still kneeling and looking up at her I could tell she was looking at the semi-hard bulge in my 501's. She made a comment something to the effect - "bet all your equipment's working fine." Handed me her business card with her home phone and said - "give me a call when you get off work."

I did and she invited me over to her house. Met me at the door in a halter and short shorts and asked if I wanted a drink. Things progressed and she ended up taking me to her bedroom, stripping my clothes and gave me one of the best bj's I'd ever experienced. Shot my wad twice before we really got down to fucking. She'd been recently separated from her husband and in retrospect, she gave me a run for the money in the hornyness department. Continued to fuck her on and off every chance I got that summer till I went back to school and she sold her house and moved out of town. Compared to the H.S. chicks, I'd dated prior to that time, she was a winner, hands down; no whining or excuses and the fact that she was experienced was a big plus. Boy, did I get an education that summer. That woman knew what she wanted. To this day, I'm a sucker (excuse the pun) for cougars tho now in my early 30's, I much prefer young 20 year-olds.

During college, I had this idea that I could make a good living or at least have some fun being a gigolo. I got started by volunteering to tend bar at local charity events. If you were willing to work for free, it was easy to get the gigs.

The plan worked to a tee. I've always been a flirt and was able to connect with attractive, well-to-do, older women with no problem. The only problem was I wasn't very good at asking for gifts. I "earned" room serivce meals and drinks from hotel mini bars. The only other thing got was "training" in learning to take love making slow.

Oh yeah, I was around 15 years. My friend's mother came onto me. She was late 20s early 30s, recently divorced, had her own business, beauty shop. She gave me lessons over about a year. Lots of fun for a youngster. She seemed to enjoy too. Anyway, you've heard what goes around comes around. Now my wife has a boyfriend 30 years her junior, legal age. So, life goes on and this older woman younger man scenario continues with many.

VerifiedGold Member

Looking back on what I described above, I really appreciate having been taught a lot about sex by an older woman, namely the fine art of eating pussy along with a variety of positions aimed at pleasing a partner. I know the first time that I went down on her, I couldn't help wondering how many other cocks had pounded that sweet piece of ass. Guess that only made me want to prove to her that I was every bit as good as those that had preceded me.

Gold Member

My neighbor was in her early 30s, with a husband who worked way too hard. I was 15 or so. I worked hard on her yard, and did a good job, I think. Plus, we had sex... which was just G R E A T. From her I learned patience, and to take my time, and just because my cock was hard didn't mean I had to try to make it go soft that minute. It was way different than fumbling around with kids my own age. And we even got naked before we had sex!

VerifiedGold Member

I was 21 and she was 31 and she had 4 kids as well. Should have been a sign but she was the woman who told me i had a big cock and she was the one that really showed me what sex was about. I was at the time the most amazing sex i'd ever had, from the dressing up, to the oral at the drop of a hat to the point i got introduced to her friends and finally she got crazy destructive and i swear i had to flee Peterborough (UK) .. Good times!

I've always wanted to experience a cougar, too shy to initiate anything though

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Well, that's the nice thing about Cougars, Sweetie...YOU don't need to worry about that initiating business...we take care of that for you. Just be prepared and not get caught like a deer in the headlights and everything will work itself out.

I dont mean to sound like a prude, but isnt this topic inappropriate because it talks about underaged sex? Actually, I dont care either way, but I do detect a bit of a double standard.

What if the ladies started up with all the underage sex they had with older guys? The mood seems to change.

Actually, there was another "sex with your teacher" thread. Most of the responses involved underaged gay experiances.
Oh well...

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Actually, I bet most older women have had that experience when they were younger. It's not like I was a "cougar" at 19 yrs old screwing 10 year olds!!!

BTW, why are you assuming we are all talking about underage sex?All of my younger men are "of age" which BTW is 17 in the state where i live :wink:

Of course, I did the "older man" thing and yes, had sex with my professor and also a boss or two.

But the difference I think is that when I was a younger woman having sex with a much older man I was not thinking, "This is HOT sex" like younger guys feel when they are with older women. Instead I was thinking/feeling the "father figure" thing, the "power trip" of being with a successful man or the being "teacher's pet." No for hot sex I stuck with guys my own age.

From my own personal experience and from the numerous posts on the subject younger men/older woman is mostly about hot sex.That's the difference. No double standard.

VerifiedGold Member

Well, that's the nice thing about Cougars, Sweetie...YOU don't need to worry about that initiating business...we take care of that for you. Just be prepared and not get caught like a deer in the headlights and everything will work itself out.

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Tho, now that I'm in my early 30's and prefer young chicks, I still love being hit on at the gym by an older woman. Less complications and I've yet to meet one looking for commitments other than a good lay. In my book, COUGARS ROCK!!!

Gold Member

Well, that's the nice thing about Cougars, Sweetie...YOU don't need to worry about that initiating business...we take care of that for you. Just be prepared and not get caught like a deer in the headlights and everything will work itself out.

Who else had a "Mrs Robinson" figure in their youth. She was the prototype for the MILF for those of us that remember the Graduate more than American Pie.

Mine was a recent recent divorcee, whose daughter was dating my best friend. She was in her late 30's, but was still really pretty. She and her ex had some money and she'd used those resources to keep herself in pretty good shape.

I had been around a few times, basically stopping to pick up the daughter. When she heard that I did lawn work, she asked if I would help her get her back yard under control. She had gotten a pretty good sized house and yard in the divorce, but she hadn't really been taking care of it.

It actually took me a couple times to see where it was headed. But lemonade in the yard turned into lemonade at the table and then a beer on the couch. Yes, she actually plied me with alcohol to take a way some of my teenage nerves.

I ended up having sex with her the rest of the summer. Most of the time I had to work first. When I came back on break she had a new boyfriend and he was taking care of the yard. It was still a heck of a summer job.

I am not assuming anything. Read the posts. If 15 is the legal age of consent, then I am wrong.

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I did read the posts. Some included underage activity. Most did not. I asked why you were assuming all of us were talking about sex with minors. Emphasis on ALL. OP did not state that so, thread should not be considered inappropriate.

I wasn't the one who had the experience with the MILF but I thank her nonetheless.
A friend of mine had gotten a new job in another city so we had a "Goodbye and Good Luck" party for him. I stayed after to help him cleanup and ended up in bed with him. He was and is to this day totally straight but thanks to his Mrs. Robinson, we had a great night together.
I found out all of this back story after he had moved away:
When he was in college, he had been hit on by an older woman, a red head with big tits (which became his favorite type of woman to this day). She was his first time and guided him through the entire session of sex, telling him what to do, where to do it, how to do it, etc. She even, at one point, dressed him up in her panties, bra and stockings and had him fuck her dressed that way...which also left an imprint on him to this day.
I didn't know anything about his Mrs. Robinson that night of his goodbye party. After we finished cleaning up we were sitting on the couch and our conversation turned to sex. I could see he was getting aroused by the looks of the bulge in his shorts. I commented that he seemed to be packing and asked him if he would show it to me. Right away he unzipped his shorts and pulled his cock out of his boxers. His cock wasn't fully erect so I asked if he could make it harder for me, which he did. I never measured it but looked to be about 8.5 by 7. I'm 7 x 6 and his was bigger and thicker than me (believe me, I compared them).
I kept telling him what to do and he did everything I asked him to do that night. I'm the only guy he's ever fucked and I introduced him to the wonderful feeling of being rimmed (which he thoroughly enjoyed).
After he moved away once in awhile he would call me late at night and tell me about the women he had just fucked. Our phonecalls would end with me telling him to take his thick cock out and what to do with it. He always would come quickly so I guess it was still a turn on for him to be told what to do.
I had a great evening with him thanks to his MILF!